3-(3-bromophenylimino)indolin-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3-bromophenylimino)indolin-2-one
• 英文别名: 1,3-dihydro-3-[(3-bromophenyl)imino]-2H-indol-2-one；3-((3-Bromophenyl)imino)indolin-2-one；3-(3-bromophenyl)imino-1H-indol-2-one
• 化学式: C₁₄H₉BrN₂O
• 分子量: 301.142
• InChiKey: CZWZKAKNTORBCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 、 3-(3-bromophenylimino)indolin-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 72.25h， 以45%的产率得到7'‐bromo‐4'‐(4‐hydroxy‐3‐methoxyphenyl)‐3'‐methyl‐3',4'‐dihydro‐1'H‐spiro[indoline‐3,2'‐quinolin]‐2‐one
  参考文献：
  名称：

  3'，4'-二氢-1'H-螺（吲哚啉-3,2'-喹啉）-2-酮的制备及其抗血浆活性。

  摘要：

  通过反电子需求的氮杂-Diels-Alder反应（Povarov反应）制备了一系列的3'，4'-二氢-1'H-螺（吲哚啉-3,2'-喹啉）-2-酮。亚胺衍生自Isatin和取代的苯胺，以及富含电子的烯烃反式异丁香酚和3,4-二氢-2H-吡喃。评估了这些化合物对恶性疟原虫寄生虫的药物敏感性和耐药性形式的体外抗血浆活性。衍生自3,4-二氢-2H-吡喃的三种化合物和衍生自反异丁香酚的四种化合物在低微摩尔范围内对耐药FCR-3菌株（1.52-4.20 µM）表现出抗血浆活性。仅衍生自反式异丁香酚的化合物显示出对药物敏感的3D7菌株（1.31-1.80 µM）的抗血浆活性。

  DOI：

  10.1111/cbdd.13598
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3-(3-bromophenylimino)indolin-2-one
  参考文献：
  名称：

  Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives

  摘要：

  Herein, a series of 3‐phenyliminoindolin‐2‐one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340–3346 cm−1) bands and C=O stretching (1731–1746 cm−1). In the 1H‐NMR spectra of the compounds, N‐H protons of indoline ring were observed at 10.65–10.89 ppm generally as broad bands, and 13C‐NMR spectra of the compounds C=O were seen at 161.72–169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open‐field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5‐hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ‐induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.

  DOI：

  10.1111/cbdd.12668

文献信息

• Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-diones<i>via</i>the Staudinger reaction:<i>cis</i>- or<i>trans</i>-diastereoselectivity with different addition modes
  作者：Vadim Filatov、Maksim Kukushkin、Juliana Kuznetsova、Dmitry Skvortsov、Viktor Tafeenko、Nikolay Zyk、Alexander Majouga、Elena Beloglazkina

  DOI：10.1039/d0ra02374d

  日期：——

  A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3′-indoline]-2′,4-diones was developed based on Staudinger ketene–imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3′-indoline]-2′,4-diones were synthesized using this method. For comparison

  基于 Staudinger 烯酮-亚胺环加成反应，通过取代乙酸与 Schiff 的一锅反应，开发了一种实现生物学相关双芳基螺[氮杂环丁烷-2,3'-二氢吲哚]-2',4-二酮的新合成方法碱在草酰氯和有机碱的存在下。使用该方法合成了一系列[氮杂环丁烷-2,3'-二氢吲哚]-2',4-二酮。为了比较，使用已知技术获得相同的化合物，其中乙烯酮是由预合成的酰氯产生的。结果表明，与先前描述的程序不同，在室温下在一锅反应中使用草酰氯生成乙烯酮可以逆转螺内酰胺形成的非对映选择性。
• Solvatochromism of isatin based Schiff bases: An LSER and LFER study
  作者：Dominik Brkic、Aleksandra Bozic、Vesna Nikolic、Aleksandar Marinkovic、Hana Elshaflu、Jasmina Nikolic、Sasa Drmanic

  DOI：10.2298/jsc160119049b

  日期：——

  calculations gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on solute/solvent interactions. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions.

  已有报道，伊斯汀的衍生物具有多种生物活性。但是，到目前为止，尚无关于伊斯丁衍生物的溶剂化变色作用的报道，作为这些化合物表征的一部分，研究和与其电子结构有关可能是令人感兴趣的。线性溶剂化能量关系（LSER）用于分析溶剂对所研究的靛红衍生物即UV的最大吸收位移的影响。通过使用Kamlet-Taft模型，基于Isatin的Schiff碱。使用SSP（单个取代基参数）将线性自由能关系（LFER）应用于取代基诱导的NMR化学位移（SCS）。所获得的相关性以及理论计算结果使我们深入了解了分子构象对取代基效应传递的影响，以及溶质/溶剂相互作用。为了可视化电子密度分布并解释溶剂/溶质相互作用的起源，在分子的优化几何形状上绘制了分子静电势（MEP）表面图。
• Synthesis of (2-(Quinolin-2-yl)phenyl)carbamates by a One-Pot Friedel–Crafts Reaction/Oxidative Umpolung Aza-Grob Fragmentation Sequence
  作者：Dong Xie、Xin Xu、Sihui Long、Xiang-Ying Tang、Long Wang

  DOI：10.1021/acs.joc.2c00502

  日期：2022.6.17

  isatin-based propargyl amines prepared from isatins, terminal alkynes, and anilines, (2-(quinolin-2-yl)phenyl)carbamates were prepared by a one-pot reaction in sequence, combining the gold-catalyzed Friedel–Crafts cyclization, oxidative umpolung aza-Grob fragmentation, and nucleophilic addition. In this process, gold-catalyzed cyclization of isatin-based propargyl amines gave 1′H-spiro[indoline-3,2′-quinolin]-2-ones

  利用由靛红、末端炔烃和苯胺制备的容易获得的靛红基炔丙基胺，通过一锅法依次制备（2-（喹啉-2-基）苯基）氨基甲酸酯，结合金催化的 Friedel-工艺环化、氧化 umpolung aza-Grob 碎裂和亲核加成。在这个过程中，金催化的靛红基炔丙基胺环化得到 1' H-螺[二氢吲哚-3,2'-喹啉]-2-酮，其通过 aza-Grob 裂解被高价碘原位氧化成得到异氰基中间体2-(2-异氰酸基苯基)喹啉。随后与醇溶剂进行亲核加成，合成了(2-(喹啉-2-基)苯基)氨基甲酸酯。该程序具有操作简单、底物范围广、条件温和等特点。
• A convenient -diastereoselective synthesisof -isatin arylimines the aza-Wittig reaction
  作者：Vadim E. Filatov、Dmitrii A. Iuzabchuk、Boris N. Tarasevich、Nikolai V. Zyk、Elena K. Beloglazkina

  DOI：10.1016/j.mencom.2022.09.022

  日期：2022.9

  A general synthesis of NH-isatin N′-arylimines involves the aza-Wittig reaction of isatin and aryl azides, providing higher E-diastereoselectivity as compared to previously described methods. The procedure is applicable even to anilines which do not directly react with isatins.

  NH -靛红N' -芳基亚胺的一般合成涉及靛红和芳基叠氮化物的氮杂维蒂希反应，与先前描述的方法相比，提供更高的E -非对映选择性。该程序甚至适用于不直接与靛红反应的苯胺。
• Khan, Khalid Mohammed; Mughal, Uzma Rasool; Ambreen, Nida, Letters in drug design and discovery, 2010, vol. 7, # 10, p. 716 - 720
  作者：Khan, Khalid Mohammed、Mughal, Uzma Rasool、Ambreen, Nida、Rama, Nasim Hasan、Naz, Farzana、Perveen, Shahnaz、Choudhary, Muhammad Iqbal

  DOI：——

  日期：——